Watersoluble formaldehyde-bisul-phite amino-aryl antimony arsenic compounds



Patented Nov. 7, 1933 5 UNITED STATES WATERSOLUBLE FORMALDEHYDE BISUL PHITE AMINO-ARYL ANTIIVIONY ARSENIC COMPOUNDS Hans Schmidt, Vohwinkel, near Elberfeld, Germany, assignor to Winthrop Chemical Company, Inc., New York, N. Y., a corporation of New York No Drawing. Original application November 1,

1929, Serial No. 404,216, and in Germany November 6, 1928.

Divided and this application February 27, 1931. Serial No. 518,914

2 Claims.

The present invention relates to Water-soluble formaldehyde bisulphite amino-aryl-antimonyarsenic compounds and to a process of preparing the same.

In accordance with the present invention stable watersoluble derivatives from amino-arylantimony-arsenic compounds are obtainable by reacting upon an amino-aryl-antimony-arsenic compound with formaldehyde-bisulphite in aqueous solution. Equivalent to the reaction with formaldehyde-bisulphite is the reaction of first with formaldehyde and then with bisulphite. Amino aryl antimony arsenic compounds suitable as starting materials for the purpose of the invention are, for example, compounds of the probable general formula:

QAPIQ the benzene nuclei of which may be further substituted by monovalent substituents, for exam ple, hydroxyl groups.

When starting from compounds containing salt forming groups it will be advantageous to use the compounds in the form of a watersoluble salt, for example, an alkali metal salt. The process may be carried out at various temperatures, room temperature or slightly elevated temperatures, say temperatures of up to about C. The solution is neutralized by the addition of an alkali, such as sodium carbonate, and the new compound is precipitated by pouring the solution into a precipitant, such as methylalcohol. In case oxidizable compounds are subjected to my new process, care is to be taken, that all operations are carried out with the exclusion of air as far as possible on account of the sensitiveness to air of the startingand end-products.

My new products thus obtainable probably are formaldehyde bisulphite derivatives of the amino-aryl-antimony arsenic compounds used as starting materials. They are brownish colored powders, soluble in water, difficultly soluble in the usual organic solvents and are intended to be used for medicinal purposes in consequence of their solubility in water and their pharmaceutical activity.

The invention is illustrated by the following example, without being limited thereto:-

EmampZa-IZ grams of the stibio-arseno-compound of the probable formula HZN HOG-lawn) NH: mN .Jks OH obtainable according to the directions of German Patent No. 397,275 from 3-amino-4-hydroxy-1- phenyl-arsine and potassium antimony-bis- (1.2 dioxybenzene -3.5-disulphonate) (compare especially Example 1 of said patent) are suspended in the freshly precipitated state in about 70 com. of water, and '7 grams of formaldehyde bisulphite, dissolved in a little water, are added. After standing for several days, solution takes place. The solution is filtered, neutralized with dilute caustic soda, the product formed is precipitated by pouring into methyl alcohol, isolated and dried in a desiccator. All operations are carried out with .the greatest possible exclusion of air. A brown powder is obtained, which is readily soluble in water with a neutral reaction.

This is a devision of my copending application Ser. No. 404,216, filed November 1, 1929.

I claim:

1. The formaldehyde-bisulphite derivatives of compounds of the probable formula:

the benzene nuclei of which may be further substituted by a hydroxy group, said products being readily soluble in water, rather difficultly soluble in the usual organic solvents, displaying a thera-v peutic action.

2. The formaldehyde-bisulphite derivatives of the compound of the probable formula:

HzN

HOGAs=Slb NHz 11m As on Hogan said products being readily soluble in water,

rather difficultly soluble in the usual organic solvents, displaying a. therapeutic action.

. HANS SCHMIDT. 

